Methyl 2-(bromomethyl)-3-nitrobenzoate → 2-[[(Amino)(imino)methyl]thiomethyl]-3-nitrobenzoic acid, methyl ester, hydrobromide

HRID 648849Notes

Reaction equation

HRID 648849 reaction equation
[Br:1][CH2:2][C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[NH2:16][C:17]([NH2:19])=[S:18]>CO>[BrH:1].[NH2:19][C:17](=[NH:16])[S:18][CH2:2][C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateHCID 2723790Thiourea

Product 1

HCID 139376122-[[(Amino)(imino)methyl]thiomethyl]-3-nitrobenzoic acid, methyl ester, hydrobromide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 18.8 g of the product from Example 1 and 5.2 g thiourea in 150 ml methanol was stirred at reflux temperature overnight. Removal of the solvent in vacuo yielded a viscous oil which slowly crystallized. The crude product was washed well with ethyl acetate, filtered and dried. The yield of 2-[[(amino)(imino)methyl]-3-nitrobenzoic acid, methyl ester hydrobromide, m.p. 178°-180°(dec.), was 22.6 g; NMR (CDCl3 /DMSO-d6): δ 4.0 (3H, s, CO2CH3), 4.85 (2H, s, --CH2 --), 7.6-8.35 (3H, m), 9.05 (4H, br s, NH).

Workup

  1. temperatureat reflux temperature overnight
  2. customRemoval of the solvent in vacuo
  3. customyielded a viscous oil which
  4. customslowly crystallized
  5. washThe crude product was washed well with ethyl acetate
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-bc1e7d4b5b7742498ee0c6001098b337
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

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